Phthalic Anhydride → HCID 131721873, compound

HRID 2288621Notes

Reaction equation

HRID 2288621 reaction equation
[NH2:1][CH2:2][CH2:3][C:4](=[N:6][OH:7])[NH2:5].[C:8]1(=[O:18])O[C:11](=[O:12])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12.C(N(CC)CC)C.Cl.[N:27]1([CH2:34][C:35]2[S:39][C:38]([C:40](Cl)=[O:41])=[CH:37][CH:36]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>CN1CCN(C)C1=O.[Cl-].[Na+].O>[N:27]1([CH2:34][C:35]2[S:39][C:38]([C:40]([C:9]34[CH:17]=[CH:16][CH:15]=[CH:14][CH:10]3[C:11]([N:1]([CH2:2][CH2:3][C:4](=[N:6][OH:7])[NH2:5])[C:8]4=[O:18])=[O:12])=[O:41])=[CH:37][CH:36]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

7

Reactant 4

HCID 6811Phthalic AnhydrideHCID 8471TriethylamineHCID 18699962HCID 18699962, compoundHCID 54106833HCID 54106833, compound

Product 1

HCID 131721873HCID 131721873, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 66611,3-Dimethyl-2-imidazolidinoneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

9.59 g (93.0 mM) of 3-aminopropionamidoxime was dissolved in 288 ml of 1,3-dimethyl-2-imidazolidinone, 14.46 g (97.65 mM) of phthalic anhydride was added, and the mixture was stirred at room temperature for 1 hour and then at 140° C. for 2 hours. The reaction solution was cooled to room temperature, and 15.6 ml (111.6 mM) of triethylamine and 16.4 g (55.8 mM) of 5-(hexahydro-1H-azepin-1-yl)methyl-2-thiophene carbonylchloride hydrochloride were added. The mixture was stirred -overnight at room temperature, and 720 ml of saturated brine was added. Then, the thus precipitated crystals were collected by filtration and washed with distilled water to give 19.96 g of 0-[5-(hexahydro-1H-azepin-1-yl)methyl-2-thenoyl]-3-phthalimidopropionamidoxime (79% in yield from (hexahydro-IH-azepin-1-yl)methyl-2-thiophene carbonylchloride hydrochloride).

Workup

  1. waitat 140° C. for 2 hours
  2. temperatureThe reaction solution was cooled to room temperature
  3. stirringThe mixture was stirred -overnight at room temperature
  4. filtrationThen, the thus precipitated crystals were collected by filtration
  5. washwashed with distilled water

Sources & evidence

ORD record
ord-f39065656cc94176936ef3491a1ad3d4
Source dataset
uspto-grants-2000_07
Patent number
US06090804

Reaction notes

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